Venture Capital ideas with Chris Dixon

If you missed part 1 – the big ideas from Dixon – you can find that here. This is part 2 and it’s all about venture capital.

These notes are from Shane Parrish’s conversation with Chris Dixon on the wonderful The Knowledge Project podcast.


Why should companies stay private?

Parrish asks why companies – like Uber – stay private. There are two reasons Dixon says. First, there’s plenty of money in the private markets. Huge public companies like Fidelity, have access to the private markets and companies like Uber don’t need to go public to raise money. Second, companies can keep a long term vision. The technology sector, Dixon says, perceives markets as too short term oriented.

Seed, series A, series B explained.

Dixon defines the different types of funding.

Seed funding (aka Angel) is investing in 1-2 entrepreneurs with an idea. This round might be for 1-2M$.

Series A is investing in a small team with an initial product. This round might raise 10M$.

Series B is investing in a company with some traction that needs money to grow. This round might be 20M$.

It’s helpful to know the nomenclature, but the big idea here is when Dixon talks about prorata rights. It’s briefly covered in the interview and worth expanding on here. Prorata rights are the option for a company to maintain their same funding level. If you invest 1M$ for 40% in the seed round, having prorata rights means you get a chance to invest enough to keep your 40% position during the Series A round. Here’s the key part of this, you get to but you don’t have to. Prorata rights are optionality.

Don’t take my word for it. Mark Suster wrote, “this (the prorata right) is important for nearly every institutional investor because once you have 25-50 investments being able to “follow” the investments that are working well is critical to making money.” Suster is explaining that VC’s expect some companies to do better than others – and it’s those positions that should be held on to. 

Fred Wilson, another VC, wrote much the same thing. “I think this is the single most important term anyone can negotiate for in a venture capital investment….The meta point I have come to understand about early stage investing is that a small portion of your investments produce all of the returns. In those investments, you want to own as much as you can.”

An investor – like Dixon – will only invoke their rights for companies that are doing well. This post includes other examples of optionality. To think well, we need to think about having options. 

On a post at his site Dixon writes about the Babe Ruth Effect. “Great funds lose money more often than good funds do. The best VCs funds truly do exemplify the Babe Ruth effect: they swing hard, and either hit big or miss big.”

Dixon says that about half of all a16z investments will fail, some will have moderate success, and some will be huge hits. It reminded me of what Seth Godin wrote, “it’s not always easy to measure what matters.”

VC wants a high slugging percentage. Baseball wants a high on base percentage. Different domains want to measure different things. It’s valuable to figure out what matters most.

The people or the product, the lyrics or the music.

In high school my group of friends used to argue whether the lyrics or music were more important to a song. One friend was a huge Dylan fan so he clearly favored lyrics. Another was a guitar player, he preferred the music.

Startups have a similar paradigm, the person or the product. Dixon makes it’s clear – invest in the person.

“It’s 90% people and 10% product at this state (Series A),” Dixon says. “At this point we know that the idea will change.” 

Dixon explains that when Dropbox was founded in 2007, mobile wasn’t a thing. The company was founded to share documents between computers. Things changed. Dixon expects to pivot and looks for opportunities with good people. But sometimes things go bad. 

Identifying failures.

“Some reasonable percentage of time the entrepreneur does everything right and things happen,” Dixon says. Google releases a competing product. The FDA rejects an application. Stuff happens. The hard part is figuring out what was due to luck and what was skill.

Michael Mauboussin provides a good framework to dismantle skill and luck. The more purposefully you can lose, Mauboussin said, the more skill is involved.

Imagine a tennis match. I could easily return each serve out of bounds and lose. Tennis is heavily skill based.

Now imagine investments. I could pick stocks that I thought were bad and maybe win or maybe lose. There’s more luck in stock picking than tennis. Some stocks labelled “sell/bad” outperform those labeled “buy/good.”*

Finally, imagine a slot machine. I could pull on the lever all day, chanting mantras and burning incense and nothing would change the odds. That’s all luck.


To successfully identify an outcome as skill or luck one needs to figure out where on the spectrum they are.

Dixon cleans up the situation with what he calls “Founder-Market fit.” That’s too much jargon for this site. We’ll call it “The Nic Cage effect.”

The Nic Cage effect.

I always wondered how Nicolas Cage didn’t make good movies. He won an Academy Award early in his career! Doesn’t that mean he’s a good actor? No, it means he was a good actor in that roll.

There are great actors for sure – Meryl Streep we’re looking at you – but a lot of it is about matching the person and the roll. I disliked Amy Poehler on Saturday Night Live, but Leslie Knope on Parks and Rec is my favorite character of all time. 

That’s what Dixon look for. He says there are three ways founders fit well.

The technical founder. Dixon says that technical expertise (coding) is one way a founder can be good. The business aspects, Dixon says, someone can learn on the job, but not the other way around. Both Jimmy Wales and Mark Cuban are examples of this.

The domain expertise. Other founders can have a deep understanding of their industry. This is the case of Alex Blumberg of Gimlet Media and Dick Yuengling of Yuengling Beer. 

The cultural movement founder. The final type of successful founder is one who’s part of a movement. Dixon says that the Airbnb founders fit this mode. Matt Barrie fit the freelancing movement. 

If a founder fits, Dixon has another filter, the maze.

The question is, what do you do in the maze?

Dixon says successful entrepreneurship figure out the maze. In startups there will be moments of confusion, disorientation, and wanting to resign. Really obsessed founders, says Dixon, will have thought about these dead ends and considered options for what to do next. And there are always dead ends.

“I’ve almost never been involved with a company that didn’t have moments of almost failure,” says Dixon.

That Dixon uses the analogy of the maze is interesting. A lot of successful people reframe challenges into puzzles, situations into games. In Surely You’re Joking Mr. Feynman, Richard Feynman said he couldn’t “do” good physics. But when he decided to “play with physics,” “it was like uncorking a bottle.”

Ray Dalio writes about this in Principles:

“I learned that there is an incredible beauty to mistakes, because embedded in each mistake is a puzzle, and a gem that I could get if I solved it, i.e., a principle that I could use to reduce my mistakes in the future.”

Many people use games as a filter to make solving problems fun. If you want more on that try Jane McGonigal’s book; Reality is Broken.

Thanks for reading, I’m @mikedariano on Twitter.

*One year ago (September 2014), ⅓ of financial analysts had “Sell” ratings for Clorox (CLX) and Campbell Soup (CPB). If you wanted to sabotage a portfolio that seems like a good place to start. But you’d only sabotage your success, because those stock soared. Those stucks are up 26% and 18%.


5 Things I Learned From Chris Dixon

Chris Dixon (@CDixon) joined Shane Parrish (@farnamstreet) on The Knowledge Project podcast to talk about venture capital, private companies, and how Silicon valley works. I found Dixon well spoken, warm, and a really smart guy. These notes will be in two parts. Part one – this part – is 5 things I learned from Dixon. Part two will be all about the weeds of venture capital.

Our table of contents looks like this; modes of workmental models meets physical psychesmaybe a16z should be z16aautomation (explained by dinosaurs)the 3rd good use of Twittera reading list.


Modes of work.

Dixon, like others, defines his work in terms of modes. One mode is meeting with entrepreneurs that a16z might invest with, another is to work with entrepreneurs they’ve already invested in. “It’s a lot of meetings,” Dixon says.

He mentions the Paul Graham post, Maker’s Schedule, Manager’s Schedule as an example of how his career has changed. Dixon began as a coder and followed a maker schedule. Now he’s a manager. Graham writes that the manager schedule is what we tend to think of, one with hour sized blocks to be filled. Makers on the other hand, think in terms of half a day or full days for their work. This creates a problem Graham writes:

“I find one meeting can sometimes affect a whole day. A meeting commonly blows at least half a day, by breaking up a morning or afternoon. But in addition there’s sometimes a cascading effect. If I know the afternoon is going to be broken up, I’m slightly less likely to start something ambitious in the morning. I know this may sound oversensitive, but if you’re a maker, think of your own case. Don’t your spirits rise at the thought of having an entire day free to work, with no appointments at all?”

Creatives work around this using modes of work (h/t to @MikeVardy for sharing this term).

Adam McKay talked about this when he spoke on the Slate’s Working podcast. John August said the same thing about writing. Neil Gaiman trots off to the woods to write. Stephen King also outlines his modes of work. The book Daily Rituals has many examples of makers who carve out time for modes.

Each makers has found that their best work happens in large chunks, and they structure time for those as best they can. Graham notes – and Dixon lives – the challenges of a manager.

Mental models meets physical psyches.

Silicon Valley is great, says Dixon, but it’s not the only place you can make stuff. 

“What’s great about places like New York and Los Angeles is you’re surrounded with people in the arts and media and all kinds of different industries, and that creates a different creative dynamic,” says Dixon.

The value of mental models has been trumpeted by many. Tren Griffin and Michael Mauboussin speak about mental models quite a bit. So does Sanjay Bakshi and  Phil Rosenthal suggests there is value in different creative outlets. 

We can also hack our way to better models. Your models plus my models equal something great than the sum of its parts. Each set is a filter that further refines ideas. 

Dixon suggests another hack, a new place. A geographic change can help you think in new ways. Physically moving could be helpful as a change of addition or subtraction. Dixon speaks to the advantages of other points of view, Michael Mauboussin says that it might help to “quiet the cacophony of Wall Street.” Either way can work for a way to think different. About being different, how is a16z different?

Why a16z might be called z16a.

When asked why a16z has succeed Dixon says, “we flip the model and think of ourselves like a service firm.” They’re different.

Being different is paramount to success. Brett Steenbarger said, “you don’t find generic super-successful traders.” Naveen Jain advised people to ask themselves, “when everyone is thinking one way, how can you go about thinking in a slightly different way?” Casey Neistat said, “the biggest waste of energy and resources on YouTube is creators trying to copy and be exactly like someone else.” Gary Vaynerchuk says he likes to zig when everybody else will zag. 

Dixon says that a16z is different. Rather than simply invest money, they help companies along the way (hence so many meetings). They help hire people, recruit, and figure out market fits. All this has given them a competitive advantage.

When Parrish asks if they’ve seen other companies copy them, Dixon says older firms haven’t, but newer ones might. It wasn’t a significant part of the interview, but it caught my attention. Why newer but not older? 

(Begin speculation).

Dixon doesn’t get into the compensation structure (and I couldn’t find it online), but it sounds like the a16z team earns their money differently. I’m guessing they get more upside in the long run and fewer guarantees in the short. Here’s why that matters.

Existing firms that don’t have this model won’t copy it because it’ll mean a short-term dip in earnings. And people hate to lose things they already have. The psychological term for this is loss aversion and here’s how it works.

When people have something – or even imagine having it – they feel more strongly toward it. Richard Thaler did wonderful research on this. Thaler walked into his classroom and handed out coffee mugs to half the students. Then he asked the mug owners to write down what they would sell the mug for, and the non-owners to write down what they would buy the mug for. 

He collected the slips of paper and noted something interesting. They sellers wanted 2X what the buyers offered AND not a single buyer was more than a single seller. That is, no deals could have been made.

We don’t like to lose what we consider ours. Firms other than a16z face this challenge. Those employees don’t want to lose money they already have or expect to have. 

The second way that a16z successfully differentiated is that they are committed to the entrepreneurs. “Our interests are in line with entrepreneurs,” Dixon says.

It seems like a16z has “skin in the game,” which is a powerful force. Casey Neistat says that the best part of working for himself is to have ownership of the outcomes. Seth Godin commented on this as well saying, “change happens when people take the blame but giveaway the credit.” My guess is that a16z has applied this to advising entrepreneurs where others have not. It’s their competitive advantage.

(End speculation).

Automation as explained by dinosaurs.

Toward the middle of the interview Parrish asks Dixon what he thinks are some new ideas that will gain traction. (Steven Kotler and others have given their own predictions for the future.) Dixon says; virtual reality*, digital currencies, and automation are areas he thinks will be more popular.

“A lot of automation doesn’t look like automation,” Dixon says,  “it just looks like software.” Let’s pause that thought and watch this awesome video.

That video points out that we only notice bad computer graphics. Things that are awesome, that blend in naturally, we miss. It’s like when Judd Apatow and James Corden spoke about good and bad movies. If someone tries to do something unnatural it shows. That video demonstrates that the best CG, is CG we don’t even notice. It supplements the movie.

Self driving cars is a big automation goal, and we see its limits because it’s still unnatural. It’s like CG that’s trying to do too much. What we don’t remark on is checking accounts can make automatic payments. That’s good automation.


The 3rd way to use Twitter well.

Twitter can be a great tool if you use it well. Here’s what others have said:

The first way to use Twitter well is to be inspired and collaborate. Austin Kleon, John August, and Nicholas Megalis talked about the value of connnecting with other people.

The second way to use Twitter well is to check your conclusions. Jason Zweig, Tadas Viskanta, and Tren Griffin all suggested we generate conclusions from multiple perspectives, of which Twitter can be one.

The third way to use Twitter – courtesy of Dixon – is to have it work for you. “Essentially I have two thousand of the smartest people in the world finding information for me and telling me what to read,” Dixon says.

Dixon’s reading list.

Parrish ends the interview with common questions and Dixon gives a nice smattering of books to read. Dixon, like Michael Mauboussin and Malcolm Gladwell prefers physical books to digital ones. Some of his suggestions:

Godel, Escher, Bach is the one book Dixon has read that had the greatest influence in his life. “I was interested in computers since I was a kid,” Dixon says, “and this book tied together computers and philosophy and music and it really broadened my horizons.”

Anything by Daniel Dennett, Oliver Sacks, and Stephen Jay Gould is good too. “I used to read all of those popular science books,” Dixon says.

He also picked up The Martian by Andy Weir and recommends The Three-Body Problem, Elon Musk (“I thought was good,”), and Sapiens (“a really good book,”).

Thanks for reading, I’m @mikedariano on Twitter. Part 2 of the interview will be online Friday.

*One additional point that didn’t fit. When Dixon was talking about VR, he mentioned virtual tourism. My personal experiences differ from Dixon’s conclusion. Each trip leads me to a new thought, moment, or experience in a way that being online does not. The best example of this is boat captains.

I’ve been deep sea fishing (years ago) and snorkeling (2013), and both experiences included boat captains that made the trip so much more. The fisherman was gruff and funny and to my teenage self he seemed like he knew things about life I would never understand. The snorkeling crew had great British accents and told stories of the Cayman Islands we couldn’t get anywhere else. Neither of these was central to the experience, but each was a strand in the web of the experience. It seems like VR misses that. 

Traveling, as Tyler Cowen noted, is more than what you see. It’s how you feel, what you smell, and how you think. I don’t know how close VR will ever get to that.

James Corden

James Corden (@JKCorden) joined Marc Maron (@MarcMaron) on the WTF podcast. I had never listened a WTF episode until this one. Why start now? Besides the numerous suggestions from people on Twitter, this episode also answered a question I had, how did Corden become the host of the Late Late Show? I saw his announcement for the CBS show right after I had seen Corden as a singing baker in Into The Woods. He was great in the movie, but how does he go from that, to a premier American talk show? Maron gets the answer.

Our table of contents looks like this: winning with religionburn the boatstalentnon-edible organic movie postersadvice from Meryl Streepwhen to do your best workevery job is a job.


Winning with religion.

The start of their interview is all about Corden’s childhood in England. It’s interesting and includes his experience growing up in the church of the Salvation Army. As an adult, Corden’s religious beliefs have waned, but maybe for the wrong reason.

Corden tells Maron that he once asked his father about faith; “What if you die and wherever you’re going isn’t what you wanted?” Corden says, “what if it just wasn’t worth it?” 

“Well,” his father says (in the way all fathers talk to their sons) “I’ve had a great life. I’ve been able to love and do the things I wanted. But what if it all ends and I’m right, what then for you?”

What if that was the case? This gets into two big ideas.

Positive asymmetry is good.

Corden’s father has found a position with fantastic upside. A lot of people look for situations where winning is worth more than losing. Donald Trump writes about this in the terms of which buildings to buy. Nassim Taleb writes about this in terms of what dinner party to go to. Scott Adams speaks to this in terms of friends. Positive asymmetry is good.

When Corden’s dad dies, there are two options. Heaven or not heaven. The former is positive, the latter is not. That’s positive asymmetry – but it’s not the only big idea in what he said. He’s also winning now. 

Winning now.

Corden’s dad is happy now because he got to live the life he wanted. He’s not sacrificing the life now for a potential reward later. He’s living well now and living well later.

Chris Hadfield wrote about this in his book, An Astronaut’s Guide to Life on Earth. Hadfield pined to be an astronaut, but had a long road to get there. For starters, he was a Canadian and Canada didn’t have a space program. Then there was all the education, politics, training, travel, and other requirements. Hadfield considered these obstacles between him and space, and writes this:

“It’s probably not going to happen, but I should do things that keep me moving in the right direction just in case – and I should be sure those things interest me, so that whatever happens I’m happy.”

Much like Corden’s dad (I don’t know if this outcome will happen, but I should work toward it and not be miserable doing it) Hadfield created a win-win situation. Later in the book the theme continues.

“Taking the attitude that I might never get to space – and then, after I did get there, that I might never go back – helped me hold onto that feeling for more than two decades.”

It’s hard to get asymmetrical upsides and winning now at the same time – but if we can it’s beautiful.

At the end of the interview, Corden says about his contract with CBS, “they can sack me, but I can’t leave.” That’s winning now without the upside. How Corden got there is worth looking at.

Burn the boats, we are here.

The story goes that when Cortes landed in Mexico with his conquistadors he ordered the ships burned so that there was no other option. This is a powerful force, and one Corden used.

“There was nothing else,” Corden says, “I just wanted to perform.” To this Maron adds, “if you have a plan B, you’re just a hobbyist.” 

In Sick in the Head, Jordan Peele says this:

“When I moved to Chicago, I was like, All right, I want to be a sketch comedian and my power is going to be in the fact that I’m going to dedicate myself completely. There’s not going to be a fallback, you know? I’m going to watch people give up and I’ll still be there, learning from it all, and if I stay with it, I’ll be successful.”

Jim Norton attributed his success to having no other options. Casey Neistat didn’t have options either. It was make it or bust. And this might be good. NPR’s Hidden Brain podcast did an episode about backup plans. The conclusion? If you have a backup plan, “there’s a downside we might not be appreciating.”

There’s a silver lining, the bar to make it is low. If you want to be an actor, and you earn enough money to eat then you made it, says Corden. “You’re one of the lucky ones.” And we don’t need much.

Mark Cuban was willing to live like a college student to “make it.” Penn Jillette lived out of his car to “make it.” Kevin Kelly noted that we need little to “make it.” Jay Leno did stand-up at retirement homes and worked as a Mercedes Benz mechanic to “make it.”

Have the right mindset, a lower bar, and limited needs and you have the recipe to “make it” too. There’s just a pinch more of something you’ll need.


You can’t just “make it.” You need talent too. “Raw talent will always get a shot,” Corden tells Maron. “You have to have an ability.” 

Adam Davidson and Taylor Pearson both spoke about the meritocracy we now live in. Tyler Cowen dedicated part of Average is Over to this idea. Now that gatekeepers are gone, if you have talent you’ll get a chance.

Today skill matters more than ever and it’s easy to see who has it. You need to figure out how this relates to you. “If you recognize your talent, that helps,” Maron says. You have to manage yourself.

Management of self.

Michael Lombardi said that the hardest form of management is self management. To know when, what, and how to change. The super successful people here are able to do that. 

Malcolm Gladwell manages his talent by waiting for something that strikes him as “novel and cool,” to write about.

Seth Rogen and Evan Goldberg manage their talent by remembering that their best skill is writing and to always return to that.

Rich Roll manages his talent by building a life that directs his addictive personality to healthy things.

Okay, that’s great that they can do that, but how do you and I do it?

How do you build talent through self management?

A – Create a volume of work under pressure. Casey Neistat, Malcolm Gladwell, and Amy Schumer all suggest to do a lot of work in a small period of time with immediate deadlines. This gets you in the groove of work and builds the important skills. 

B – Be you. You can imitate someone at first, even remix their work, but eventually you have to be you. In On Writing, Stephen King writes:

“Stylistic imitation is one thing, a perfectly honorable way to get started as a writer (and impossible to avoid, really; some sort of imitation marks each new stage of a writer’s development), but one cannot imitate a writer’s approach to a particular genre, no matter how simple what that writer is doing may seem. You can’t aim a book like a cruise missile, in other other words.”

C – Have a community. Each time Corden elaborates on part of his career, it involves other people. This is true for Jamacian sprinters and Russian tennis players and comedians – groups are better to grow in.

Those are things to do, but knowing what not to do is good too. Corden has one suggestion, don’t fake it.

Non-edible organic movie posters.

Corden and Maron talk about what makes a good movie. It needs to say something they conclude. Judd Apatow writes that good movies say something,  (from Sick in the Head):

“When you see a movie that Sean Penn directs, you realize he’s not fucking around. It’s like listening to a Nirvana record or something. This is not a job. They have something to say. And in comedy, the people that we like the most, when they score, they have something to say that’s important to them.”

Corden notes, “some movies just feel like posters.” That’s faking it.

When Gary Shandling spoke to Judd Apatow he said that this is the struggle. “That’s what the struggle was in the writer’s room, in a nutshell: Getting people not to write just words.” Writing is about more than words. That superficial, fake, phoning it in. Whatever expression you favor, it digs up the same underlying idea. 

Shandling wanted writers to write the characters and emotions. Authors speak about this all the time. Stephen King (also in On Writing) says that he’s ambivalent about profanity in his books. Unless it’s true to the character. If the characters is profane, then they need to swear in the book. That’s authentic and organic to the art.

If you want to create, create something real. If you want to work well, Meryl Streep has some advice.

Work advice from Meryl Streep.

“She takes her work unbelievable seriously and she doesn’t take herself seriously at all.” – James Corden

That’s why people love Meryl Streep.

When to do your best work.


This was my curiosity. How the singing baker became a late night host. It began, Corden says, when he did the play One Man Two Guvnors in New York, 2012. Corden was the star and won a Tony Award for his work. He didn’t know it, but two CBS executives were in the audience and decided that he should do a show for them.

Most people don’t do this. Penn Jillette said that most people don’t do a good job. If you do do a good job though, people will want to watch you. Jillette says that there’s only one magic trick he does. He works harder than the audience expects him to. That’s him doing a good job. 

Louis C.K. had a similar experience making his TV show. From Sick in the Head:

“This year (2014) was a totally different experience than last season. I didn’t do it like a job. I decided I don’t need to go and try to make movies or anything. This show was a good job. It’s a good thing to be doing creatively. I had this thing that I was going to make a movie. And I’d been saving it and I said, Fuck it. I’ll make an episode out of it. So cut it into two pieces and I made an episode and it’s a whole flashback thing.”

Rather than sit on his great idea, Louis did his best work.

“Every job is a job.”

That quote is from Austin Kleon, but others have said it too. Jon Acuff said the same thing about entrepreneurship. Maron adds to this.

He recalls going on Conan one night and coming off stage, looking for the party. That’s when you realize it, Maron says, “it’s just a bunch of fucking people at work.”

There’s no dream job. Every job has something that’s not wonderful. Even Seth Rogen and Evan Goldberg felt afflicted by this, and so they installed video games in their offices.

Thanks for reading, I’m @mikedariano on Twitter. If you want to connect for work, please get in touch. If you want to say thanks, here’s a place you can donate. 

One final note, I promise that not all posts will have so many references to Judd Apatow’s book, Sick in the Head. But I just finished it and it was great.

Eight (more) things I’ve Learned from Judd Apatow

This is part two of 8 things I learned from Judd Apatow. All of the quotes are from Apatow’s book, Sick in the Head. If you want Part 1, it’s here.


Lifestyle creep.

“I didn’t have a lifestyle to maintain.” – Jay Leno, 1984

Leno says that when he graduated college – with hardly any stand-up experience – he would work anywhere. That included retirement communities. “I would drive hundreds and hundreds of miles to work for free for four or five minutes,” Leno says. It didn’t matter, he made 30-40 bucks a week and that was enough. “I didn’t have a lifestyle to maintain.”

If you have the luxury of not needing luxuries, it lets you spend a lot more time creating something. Penn Jillette slept in his car while he worked the streets of Las Vegas. He didnt care. It was enough that he could perform.

Mark Cuban said the same thing. He lived  cheaply, and was willing to retire cheaply. “I was willing to live like a college student,” Cuban says about his mindset at the time. All Cuban wanted was an American Airlines lifetime pass and the time to use it.

Maintaining a lifestyle reduces optionality. Remember how Part 1 started? Jerry Seinfeld said, “Quality. That’s my only real consideration.”  If he needed to make money, he would have needed to take any job. Leno leveraged the same idea.

Diminishing returns.

“And the thing is, Are you willing to compromise quality to keep it going? Of course, the answer to that was no. And that’s why the show ended when it did.” – Jerry Seinfeld, 2014

The hardest part is starting. But it gets immediately easier. Going from one to two is easy, two to three a smaller challenge. And so on.

Seinfeld tells Apatow it was physically hard to make the show. Add in the challenge of making it better and you reach a certain point of resistance.

It’s true beyond television. People losing weight see this all the time. Starting is hard, but the easiest pounds are the first ones. It’s true for fat cats in the same way it’s true for belly fat. This is from When Genius Failed, the book about a hedge fund that failed because of diminishing returns (of good options to invest in):

“By now Long-Term was succumbing to the fatal temptation to put its money someplace. In a clear speculation, it bet on the U.S. stock market to decline, via options.”

The story of hedge fund Long Term Capital Management (LTCM) is one of diminishing returns. There were only so many great investments that could return 18% or 34% – and they found them. They succeeded brilliantly. Investors came with money. Then things got harder.


“Our morning meetings start at nine. We have to pitch out our ideas – and in some ways that is the challenge of a show. It’s to create a factory that doesn’t kill inspiration and imagination. You try to create a process that includes all the aspects of a mechanized process that we recognize as soul killing, while not actually killing souls.” – Jon Stewart, 2014

Apatow had asked Stewart how they were able to create The Daily Show everyday. A good process is key for creative people, a mold that allows wiggle room. It’s why so many creatives have daily rituals.

Mason Currey curated a delightful collection of these in the book, Daily Rituals. Two excerpts from there. First, George Orwell needed a job to supplement his writing income:

“The post at Booklovers’ Corner proved an ideal for for the thirty-one-year-old bachelor. Waking at 7:00, Orwell went to open the shop at 8:45 and stayed there for an hour. Then he had free time until 2:00, when he would return to the shop and work until 6:30. This left him almost four and a half hours of writing time in the morning and early afternoon, which conveniently, were the times that he was most mentally alert. And with his writing day behind him, he could happily yawn through the long afternoons in the shop and look forward to free time in the evening.”

And this from the routine of Ingmar Bergman.

“There (his home in Sweden) he followed essentially the same schedule for decades: up at 8:00, writing from 9:00 until noon, then an austere meal. ‘He constantly eats the same lunch,’ the actress Bibi Andersson remembered…After lunch, Bergman worked again from 1:00 to 3:00, then slept for an hour. In the later afternoon he went for a walk or took the ferry to a neighboring island to pick up the newspaper and the mail. In the evening he read, saw friends, screened movie from his large collection, or watched TV.”

If you want a modern version, listen to Adam McKay on Slate’s working podcast or read The Habitual Hustler.

When you start, your work sucks.

“I remember feeling like, Oh no, I can’t do that. I just watched some magic right there. It was a gut-wrenching feeling.” – Peele, 2014

That’s what happened when Peele showed up at Second City in Chicago. And, this was right after Amy Poehler, Steve Carell, and Stephen Colbert had left. Peele wanted to be in the major leagues, saw a AA fastball, and knew he couldn’t hit it.

At the start you should get comfortable with being bad.

Austin Kleon noted this too. “There’s a big gap when you’re starting out between what you love and what you’re producing.” The only thing to do is get better. Apatow’s interviews began this way. “I want to do that,” Apatow thought, “how do I do that?” He didn’t know, so he started asking. That was the premise of interviewing comedians as a high schooler. He wanted to know how to do their job.

What did Jordan do? He figured that if he couldn’t make the quality, he’d provide the quantity.

“When I moved to Chicago, I was like, alright, I want to be a sketch comedian and my power is going to be in the fact that I’m going to dedicate myself completely. There’s not going to be a fallback, you know? I’m going to watch people give up and I’ll still be there, learning from it all, and if I stay with it, I’ll be successful.”

The religion of work.

“I’d always wanted to be a person who worked so much that I wasn’t even available to go to dinner.” – Lena Dunham 2014

You can like work. It’s okay. Casey Neistat told Tim Ferriss, “I believe in the religion of work.” Tyler Cowen commented that maybe you don’t need happiness. Maybe you need work, to eat well, and have a stable home life. That can be a full life too.

Louis C.K. on a knife’s edge.

Louis C.K. was so close to being unknown. So, so close. He was a high school dropout. He worked at a fried chicken restaurant. He smoked dope and drank beer.

The comedian we see today, the guy who can do everything was nowhere to be seen when Louis was young. The guy who can release his own special and make so much money he gives most of it away was this close to being the guy who said, “Welcome to KFC.”

So what changed?

When Louis was in high school his mom went to a parent teacher meeting at school and was told that her son dropped out. When asked why, Louis said he just didn’t care about school. “So what will get you to care?” asked Louis’s homeroom teacher. “TV. Movies.” Louis said.

The next day Louis showed up and his teacher handed him a business card for the local TV station. “It won’t pay well,” the teacher said, “but they take kids your age.” “I had direction in my life,” Louis tells Apatow.

Louis fixed equipment. He learned to edit. How to shoot and write and do all the behind the scenes stuff. All the stuff that he does now is possible because he cut his teeth on it as a high school student. And it almost never happened.

What if Louis hadn’t shown up for that meeting, or if the teacher hadn’t? What if the teacher had a bad day and thought, this kid doesn’t care? If the TV station had enough interns? If Louis never showed up at the station? If someone there had a bad day and said ‘get the hell out’?

That’s how closely Louis came to not being Louis C.K.

Look for ‘organic’ as a signal in the noise.

“When you see a movie that Sean Penn directs, you realize he’s not fucking around. It’s like listening to a Nirvana record or something. This is not a job. They have something to say. And in comedy, the people that we like the most, when they score, they have something to say that’s important to them. And to me, that’s what I’m always looking for.” – Judd Apatow, 2010

That’s from Marc Maron’s interview with Apatow. It’s fantastic. I’m looking forward to more Maron interviews and this one is why. Maron and Apatow cover a lot of good ground. It’s emotional. It’s funny. It’s humanizing.

The lesson in this quote is to create something real. Not linkbait. Not slideshows. Something that speaks a truth.

One of the macro themes in the book is that the comedians don’t succeed until they find their true voice. That’s what Casey Neistat told Tim Ferriss about making YouTube videos. It’s what Arthur Samberg told Barry Ritholtz about investing. Brett Steenbarger said, “you don’t find generic super-successful traders.” It’s what Peter Thiel wrote about in Zero to One.

If you do something creative, it needs to be done by you and for you. Anything else won’t work.

Roseanne Barr and Jim Carrey.

This is personal. I remember flipping past Roseanne on TV in the early 1990’s and thought, how can anyone watch that. She’s a jerk, a diva, loud and obnoxious. (Carrey I thought was okay, though not that funny)

I was so wrong.

Roseanne Barr may have been those things, but not without reason. Of all the people in the book, it’s her interview with Apatow that left me with “the feelz.”

Jim Carrey too. Apatow recalls this story:

“Jim Carrey always used to say that when he saw homeless people he would have this image of the guy patting the ground going, “Here, this spots for you.” That gave me chills.

Carrey dropped out of high school because he had to help his dad clean buildings. To earn money for their family. It wasn’t enough, and they became homeless.

People are complex. They aren’t jerks or divas or loud and obnoxious without reasons. They may not have good reasons – though Roseanne had some good ones – but they are reasons. If I want to connect with a person, I need to understand that. People are always serving some interest or habit and there’s a sequence that led to that.

There’s humanity in everyone and the people who seem like they need it the most get it the least. Roseanne had a terrible childhood. A difficult adulthood. An uphill professional situation. None of it was good, and neither was Roseanne.

Roseanne got crapped on by a lot of people. She’s not blameless, but she almost certainly got more than she deserved. This chapter reminded me to be empathetic. To be kind. To love others.

Someone who I never thought about was someone who reminded me to think about others.

Thanks Roseanne.

Thank you for reading, I’m @mikedariano on Twitter.

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Update: An earlier version of this post has “starting” misspelled as “staring.” Thank you Rhett for the heads up.

Eight things I’ve Learned from Judd Apatow (Part1)

Judd Apatow is six shades of wonderful. His lovely conversation with Bill Simmons inspired me to get his book; Sick in the Head: Conversations About Life and Comedy. The book is funny and tender and full of life lessons.

Judd Apatow fascinates me. Whether it’s seeing his work (Girls, 40-Year-Old Virgin), hearing people (Seth Rogen and Evan Goldberg) talk about him, or reading his book (Sick in the Head) – I can’t get enough. Here are 8 things I learned from Judd Apatow. 

One note: This is Part 1 of 2, and the format of this post is inspired by the posts Tren Griffin does at 25IQ.


Optionality is a powerful force of life. Scott Adams compared it to playing slots, except the machine of life doesn’t require money. “I find it helpful to see the world as a slot machine that doesn’t ask you to put money in. All it asks is your time, focus, and energy to pull the handle over and over.”

In 1983, Apatow interviewed Jerry Seinfeld and asked what he was going to do next. “Quality. That’s my only real consideration. It could be anything as long as the people are trying to do something good. I don’t want to do a piece of junk. I’m not starving you know.”

Seinfeld was thinking about optionality, and a lot of other people do too:

A – Charlie Munger and Warren Buffett wait for investments with large upsides.

B – Nassim Taleb thinks about options for his investments, but also his dinner choices. “The most interesting options,” Taleb writes in Antifragile, “are free, or at worst, cheap.” p175

C – Donald Trump writes in The Art of The Deal that a good property has to be purchased for a good price. And then, “it takes almost the same amount of energy to manage 50 unites as it does 1200 – except that with 1200 you have a much bigger upside.” p57

D –  B.H. Liddell Hart wrote “The classic book on military strategy” and concluded that optionality was the main ingredient for victory.

Boot camp.

“(The Last Comic Standing Tour),was like boot camp.” – Amy Schumer, 2014

Apatow talks to Schumer about being a female comedian and she has a lot of good things to say. Not that things are good but good to know. I think Schumer is wonderful and I’m glad she’s in the book.

She also touches on something both Malcolm Gladwell and Casey Neistat suggest; volume under pressure. You need a certain volume of work under pressure to develop your skills. In the same way that carbon accumulates under pressure to form a diamond, valuable skills can be created the same way.

Boot camp isn’t glamorous. David Levien said, “it seems brutal when you’re toiling away in obscurity.” But it’s work that needs done. 

Stand still, walk, or run.

“It’s almost impossible to keep success going because you have to stop at some point to rest and learn something new.” – Chris Rock, 2014

One challenge of stand-up, said Rock, was filling up your tank. You need to have a life that you can talk about in your act, he tells Apatow. But if you constantly do your act, you don’t have a life.

Michael Lombardi told Shane Parrish that this is a huge challenge in the NFL too. Everyone there is running, and to get ahead you need to run faster. That’s tough, there’s no time to learn something new.

Casey Neistat made this video which explains this idea::

The spark.

“I just try to always remember where that initial spark came from. It’s like a pilot light, and you try to make sure it doesn’t go out.” – Eddie Vedder, 2013

Vedder tells Apatow how he tries to remember where his start. His muse. His catalyst. That was the energy state that started the ball rolling.

For a lot of comedians in the book it’s fear and pain. Seinfeld stands out as one of the few interviewees that doesn’t emotionally pull the reader. I felt like I wanted to hug everyone – including Rosanne. Even Apatow has these feelings. Jim Carrey has the strongest ones (that will be in part 2). If your spark is dark, it’s hard to get past it. 

Dayenu (it would have been enough).

“If it never happens again, I’m okay with that. At least it happened once.” – Apatow about Freaks and Geeks. 2013

This was a tender part of the book. If you have a kid, and they lose their favorite stuffed animal, you understand a sliver of Apatow’s Freaks and Geeks experience. Apatow was very open about it during his podcast with Bill Simmons. He loved those people. It’s why he kept working with so many of them. It was a family.

Now Apatow has the comfort of understanding that moment. He understands, as Phil Rosenthal noted, Dayenu. Rosenthal said that at any point in his career, “it would have been enough.” Rosenthal sounded at peace and only years (decades?) later, Apatow feels the same way.


Garry Shandling hosted the Tonight Show for the first time thanks to luck. The first choice, Albert Brooks, got sick 24 hours before he was set to host.  

Jason Zweig said his writing opportunities were based on luck. It’s part of Scott Adams’s moist robot theory: “If you control the inputs, you can determine the outcomes, give or take some luck. Eat right, exercise, think positively, learn as much as possible, and stay out of jail, and good things can happen.”

Mark Cuban and Seth Godin both cashed out before the dot com crash and admit they got lucky. Trip Adler says that at Y-Combinator he was told his idea for a ride sharing app wouldn’t work. It was 3 years before Uber.

Luck matters. “I’ve thrown a lot of darts and I don’t necessarily take credit,” said Naval Ravikant “a lot of it was luck.”

My favorite day of the week.

“The good time movie for me has been every single one of them.” – Harold Ramis 2005

For a guy that worked with Bill Murray, Chevy Chase, and John Belushi, and with Second City, Ramis has so many great sources to pick from. But he appreciates the moment – something Naval Ravikant is trying to do more of. That’s all we have is the moments.

His comments about movies reminded me of this moment from Winnie the Pooh:


“What day is it,” asked Pooh.

“It’s today,” squeaked Piglet.

“My favorite day,” said Pooh.


“I’m trying to fuck my kids up just enough so the’ll want to get a job.” – Judd Apatow 2014

Apatow talks with James L. Brooks about life and death and comedy. His comments come after telling Brooks about his life growing up and why he worked so hard when he was young. As a kid he saw his parents go through a nasty divorce (his mom charged 30K$ to his father’s credit card) and Apatow realized he had to earn money.

Apatow worked really hard. What’s noticeable about his early interviews was how young he was. From interviewing Seinfeld as a high schooler to being the youngest writer for Garry Shandling, Apatow was the youngest at everything. He worked hard because he had to.

This challenge is good. In The Obstacle is The Way, Ryan Holiday examines situations where different people succeed despite the challenges. Holiday writes this: Before he was an oilman, John D. Rockefeller was a bookkeeper and aspiring investor— a small-time financier in Cleveland, Ohio. The son of an alcoholic criminal who’d abandoned his family, the young Rockefeller took his first job in 1855 at the age of sixteen (a day he celebrated as “Job Day” for the rest of his life).”

Apatow wants some of this for his daughters. Some resistance, some obstacles.

Part 2 will be out Friday.

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John August

John August (@JohnAugust) was on The Writer Files podcast with Kelton Reid (@KeltonReid). This was a new podcast for me – and it was pretty good. First, there is a lot of writer-ness here, but also some great macro ideas for anyone. Here’s what we’ll cover:

  • See it to achieve it.
  • The balance of depth and breadth.
  • August’s 2 productivity hacks.
  • Writer’s block (proliferated by a writer’s bloc).
  • General writing tips.


See it to achieve it.

Until Phil Rosenthal and Judah Friedlander praised litterally seeing comedians, I didn’t think about how important this was. It’s really important. August adds this to the idea of seeing is the first step of achieving:

“It sounds really naive, but before the internet it was hard to know how movies were made or how things got written. So it was while I was at Drake that I realized, ‘oh my gosh’ people write movies and I should do that.”

August applied to graduate school at USC and started soon after began his career. 

As August points out, the internet has made this process a lot easier. One tool is Twitter. The people I’ve written about have mentioned two specific ways to use Twitter. The first, is to use Twitter to debunk your opinions.

We stink at realizing when we’re wrong. We often fall for the psychological misstep, “confirmation bias.” We’ll look for things we already agree with. Tadas Viskanta noted that Twitter can be used to fix this error. Expose yourself to contrary opinions he advised. Jason Zweig said, “feed yourself as much disconfirmation as you can.”  Proving yourself wrong is good.

Jeff Bezos praised the value of changing your mind. Maria Popova calls it an “uncomfortable luxury.” About this Tren Griffin quotes Charlie Munger, “Munger likes to say that a year in which you do not change your mind on some big idea that is important to you is a wasted year.”

The second way to use Twitter well is to connected to people who show you what is possible (see it to achieve it). August uses Twitter to promote writing sprints. 

This kind of association, even digitally, can be helpful. Austin Kleon is a fan of our digital connections. Nicholas Megalis said that work is so much easier now because of the internet. 

See it to achieve it is a great slogan – it’s catchy and it rhymes. But I left out the hard middle. The place where you need to build a depth and breadth of skills. Something August has done. 

The balance of depth and breadth.

“There are parallels between journalism and screenwriting,” August says. He doesn’t explicitly point them out, but it’s enough to note that he does. People in creative fields praise folding in other domains. In the same way that chocolate is better with peanut butter, writing is better with other writing. 

 Phil Rosenthal, Judd Apatow, and Brian Koppelman all suggest that people do work in areas beside their main one. The Marc Maron and James Corden interview has this suggestion as well.

August adds his name to the collection of people with this suggestion. He created the Weekend Read app to better read screenplays and scripts. It’s helpful, he says, “to see what movies look like in their non-screen form.” This is a way to expand ones point of view. The most successful people combine a wide range of skills, ideas, and connections to form the base of their creativity cumulation.

But you have to come back to one thing. Seth Rogen and Evan Goldberg said that directing and producing movies was great, but they had to return to writing. “That’s our homebase,” Rogen said.

Judah Friedlander is someone who admits that he’s in the middle of this process. He’s written books, for a TV show, and done some stand-up. He has a good base. His next step is to do a stand-up special.

August is at a certain level – his next project is for Disney – so how did he get there?

August’s 2 productivity hacks.

1 – August says that his daily balance of work, “depends on where I’m at.” He understands that different stages of projects require different types of work. Adam McKay spoke about this on Slate’s Working podcast. “I spend the first couple of hours identifying what I have to do,” McKay says. “If you don’t identify what you have to do, it feels overwhelming.”

It sounds like August has a similar system for work. If he’s exploring a new project it might take eight hours of wandering. This is good. “The process of research,” August says, “is what usually reveals the interesting things.”

August is echoing Maria Popova who said,

“I just had tea with someone – a writer whose book I’d written about and who reached out and wanted to connect – and that hour-long conversation gave me a dozen ideas to think about, to learn about, and thus to write about (including two books I already ordered based on our chat). Is that “research” in the sense that one deliberately sets out to find something already of interest? No. Is it “research” in terms of the unguided curiosity that lets one discover something previously unknown and succumb to the intellectual restlessness of wanting to learn everything about it? Absolutely.”

She continued:

“And I think that’s part of our challenge today, not just semantically but also practically – we tend to conflate “research” with search, which is always driven by looking for something you already know you’re interested in; but I think the richest “research” is driven by discovery, that intersection of curiosity and serendipity that lets you expand your intellectual and creative comfort zone beyond what you already knew you were looking for.”

2 – August knows how he needs to work. “I try to get something done in the morning, then do less important things during midday,” August says, ”and maybe one more writing sprint at night.”

To know when your energy levels will be higher or lower, or your focus will change is a key understanding for many writers. Malcolm Gladwell noted his understanding in regards to research. Tren Griffin said it’s important to know if you are someone who builds things or notices them.  Rich Roll transformed his life once he understood his tendencies.

August has settled into a good groove. He defines his work and knows the best way to do it. There’s one more thing we should address – August being a writer and all – writer’s block.

Writer’s block.

“You just have to do it,” says August. Seth Rogen and Evan Goldberg both addressed this: “writer’s block is a term people give for bad weeks,” Goldberg said. “It’s when they lose inspiration,” Rogen added.

Anne Lamott writes that it’s not so much a block as a chasm, “the word block suggests that you are constipated or stuck, when the truth is that you’re empty.”

It’s one thing to just say, “do the work,” but, if it was that easy you would have done it. If you have writer’s block here are a few idea for getting unblocked (or crossing the chasm).

A – August created, the Writer’s Emergency Pack, to, “Fix plot holes. Spice up stock characters. Rethink your themes.”

B – Brett Steenbarger said that creativity is a mix of analyzing and synthesizing. That is, figure out the details about a situation, then look around to see where that knowledge hasn’t been applied.

C – Penn Jillette said to create what you hate. That’s the thing you can make better he said.

D – Casey Neistat, Kevin Kelly and J.K. Rowling all found creativity in scarcity.

E – Cal Newport is more creative out of the office.  

“Creativity,” August says, “is the ability to picture something that doesn’t exist and find ways to make that exist.”

Writer’s tips.

The podcast had a nice conversation about different writing things. Here’s a few that stood out to me:

– One of August’s favorite is this from Stephen King, “the road to hell is paved with adverbs.” It’s from King’s wonderful book, On Writing. Though one author already mentioned in this post used adverbs royally. I’ll let you inquire who.

– What makes a good writer?  “It’s not bigger words,” August says, “it’s ways to describe emotional truths.” It’s verbs, great writers have a phalanx of verbs ready to spring into action.

– Good characters, August says, have a clear circumference of what they’re going after. He mentions both Sherlock Holmes and James Bond as some of his favorites, and I need to add one more. The best character, with goals so clear they could be a jewelry store window (which he would probably throw someone through) is Jack Reacher. Malcolm Gladwell explains why.

– August prefers the Kindle for one-off books, but physical copies when he’s revisiting something. “There’s a sense of geography in a printed book that’s really helpful,” August says. Michael Mauboussin said the same thing in his interview.

– August says that he writes by hand to avoid correcting something he’s written. It’s easier to hit the backspace key than erase. This is a good example of how small barriers can stop an action. Tiny obstacles can help us stop us from snacking or make better financial choices.

– August also praises traveling to locations to get into the spirit of the place. Tyler Cowen spoke about the advantages of travel. So does Stephen King in the aforementioned book. Robert Kurson does too. 

If you want more about writers and writing you may enjoy these posts; Simon Rich, Malcolm Gladwell, Robert Green, or Steven Kotler.

Thanks for reading, I’m @mikedariano on Twitter.

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Casey Neistat

Casey Neistat (@CaseyNeistat) joined Tim Ferriss (@TFerriss) to talk about YouTube, creativity, and the value of scarcity.

I started to follow Neistat after this interview posted and dig through his archives. It felt weird kinda weird. It seems like a lot of his fans are teens, tweens, and being weaned. They’re really young. It reminded me of what Judd Apatow said about a Taylor Swift concert. You can’t seem to disinterested or too interested. You have to find the median of watching with respect.

That’s how I felt about Neistat. His videos are cool. Some are instructions (I’m watching this to learn about that I told myself). Some are less so. Some seem like too much information. I didn’t know how to feel.

Then I realized it didn’t matter. The more I thought about this, the less I cared. Neistat (like everyone else on this blog) speaks about being human. Though each person is different, their stories are largely the same.

Patrick O’Shaughnessy pointed this out in his recent (monthly and recommended) newsletter on books.

“One of Schopenhauer’s main points is that way too many authors simply summarize/synthesize what has already been written on a subject. Given the amount that I read I see this all the time. Even some books that seem very original are not at all! For example, I thought Thiel’s Zero to One was incredibly original until I read de Bono, who in turn I thought was incredibly original until I read Koestler (I’ve yet to find Koestler’s antecedent or superior). For the record I still like Thiel and de Bono, just not as much as I like Koestler.”

That’s almost exactly what this blog is! None of these stories are original. They’re all part of the same story.

It’s like music. Everyone sings in the song of life, but different people can hear different keys. Neistat resonates with people because his story is one that people can hear. Another “key for the song of life,” are the Stoics. Quotes like this resonate with me. 


It doesn’t matter who Casey Neistat’s fans are. Gary Vaynerchuk said that when a new app comes out don’t look at the foolish ways people use it (in this case he was talking about sexting). Instead, think about how you can use it well. It’s the same for the influences in your life.

If Neistat says something that resonates with me, that’s all I need to hear. So what did he say that was impactful? The importance of finding your lane, how not to not be huge on YouTube, who is successful, 2 free video creation tools, when to filter your life, a business idea, and books and movies to enjoy.

One word or warning, this post is a monster. You may want a snack. 


Find your lane. For Neistat it was a bike lane.

The start of the interview is about Neistat’s history and early career. There’s not much to point out here except that Neistat had a hard life. “I grew up in the poor part of Connecticut,” Neistat says. He ran away from home, dropped out of high school, and had a son when he was 17.

Things changed when he found filmmaking. His brother showed him an iMac and Neistat bought one too. Then things really took off when people started paying him for his work. Asking for $5,000 for a job he would do for $100 was a big moment for him.

Success – in relative terms – continued when Neistat made the video Bike Lanes. (Here’s the first of many YouTube videos on this post.)

Ferriss asks how Neistat was inspired and Casey says, “whatever I care about I make a movie about.” This, we should note.

arcreactorIf we care about something so much that we act on it, we’ve found something important. We’ve found an energy source. It’s like Arc Reactor in Iron Man.

Wayne Dyer compared it to a burning flame inside us. Gary Vaynerchuk calls it hustle. Ramit Sethi sees a positive feedback system where passion feeds skill which feeds passion and so on.

Everyone who succeeds greatly says; your passion must fuel furious work.

That’s what Neistat has done. He points this out many times in the interview with Ferriss and on his YouTube Channel. Making movies, he says, is not about the gear. He started to make films with the simplest equipment and the most basic software. Those are the surface parts of storytelling, the tip of the iceberg. To make something great you need the deeper understanding. 

Look at Hollywood movies, Neistat says. They have the talent, money, gear, time, experience, and connections. They have everything you need, but it doesn’t always work out. Why does one Matt Damon movie about space (The Martian) make more than twice as much money as another (Elysium)?

When Seth Godin said this, “Stories are never about the person telling the story, they are always about the person hearing it.” That’s the type of thing you have use your passion to learn. You don’t need fancy camera gear anymore than you need a fancy blog or book or narration by someone famous. What is paramount is story.

Neistat notes that because he never graduated from film school (much less high school), he learned things his own way.  School is good, Neistat says, because it teaches you to get from A –> B. If you don’t know how though, you need to figure out your own way, and it could be an advantage.  That’s what he did. (Watch this one minute sequence, 3:34-4:44)

Neistat developed the “craftsman mindset.” Coined by Cal Newport in his book, So Good They Can’t Ignore You, it’s the focus to build valuable skills. Valuable skills, Newport writes, are the only things that get you great jobs.

When Neistat made Make it Count for Nike, the video opens with this scrolling text:

“Nike asked me to make a movie about what it means to #makeitcount. Instead of making their movie I spent the entire budget traveling around the world with my friend Max. We’d keep going until the money ran out. It took 10 days.”

That sounds great. It’s rebellious. It smells like following your passion. But it hides a bit of the truth.  That video, Neistat points out to Ferriss, was the 3rd video in a series for Nike. He had already done two video for them and this one had the “budget of what Nike usually pays for snacks and drinks.”

On the surface it looks like “follow your passion,” but it’s deeper than that. Neistat was an expert filmmaker who had existing relationships and created career capital. Neistat’s career mimics Newport’s framework so much, he could have been a case study the book. Newport writes:

“Career capital theory argues that the traits that define great work are rare and valuable, and if you want these in your working life, you must first build up rare and valuable skills to offer in return.”

Neistat worked furiously to create these skills. He’s doing this again for his company – Beme. How? Just watch what Ferriss calls “a brutal schedule.”

You don’t need to do that. You probably shouldn’t do that. Why? Because you’re not Casey Neistat. That’s his lane. Ferriss, you, me – it doesn’t matter what we do, but we have to do something different. We have to find our own lane.  Arthur Samberg noted that we are our competitive advantage. No one does you better than you.

How can you do it on YouTube?

How to not not be huge on YouTube.

Neistat has no idea how to get an enormous audience on YouTube, but he does offer something helpful – how not to be huge. Let’s break down the framework (macro idea of answering questions) here before we talk about how to gain an audience (micro idea of YouTube followers).  

What Neistat has done is invert the question, and it’s a helpful tool. Tren Griffin noted that it’s easier to solve problems by looking forward and backwards at them. Instead of asking, “how do I get a better job?” Griffin might suggest you ask, “how do I get better for my job?”

Michael Lombardi said that The New England Patriots find NFL players this way. “Scouting’s not about finding players,” Lombardi says, “Scouting is about eliminating players.”

Ferriss’s question, how do you get YouTube subscribers is hard to answer. No one knows.  Neistat reverses the question and answers, how do you NOT get YouTube subscribers. 

This, Neistat says, is much easier:

“The biggest waste of energy and resources on YouTube is creators trying to copy and be exactly like someone else. The only thing that succeeds on YouTube are the people that think outside the box and do new things.”

If you want to not succeed, do what everyone else is doing. Find the lanes other people are in. 

This gives us something to work with. Knowing what not to do can be as helpful as knowing what to do. What to live a long time? Don’t smoke, drive motorcycles, or weigh more than you should. Those three don’t-dos are more helpful than any three do-do’s. 

“Trying to copy and be exactly like someone else,” almost never works. Peter Thiel notes the value of being different. Brett Steenbarger said, “you don’t find generic super-successful traders.” Lewis Howes played handball because it was different.

Being different is really important, but how do you actually do it?

Step 1: Stretch. Steven Kotler said that the best extreme athletes stretch themselves 4% past what they think is possible. These small changes add up. 

Step 2: Have wide inspirations. Neil Gaiman said that if you want to be the next Tolkien, don’t read Tolkien. 

Step 3: Remix. Austin Kleon said, “everything is a remix.” 

Step 4: Persist. Timing is impossible to nail. The only thing you can do is keeping doing it. Mark Cuban offered streaming music years too early. Trip Adler had the idea for ride sharing years too early. Neil Strauss released his book the same weekend as Hurricane Katrina. You have to survive.

Neistat has a suggestion too. The only way to find your own path is to start.” (click to tweet)

A perk of  being different is that you don’t have to be that good. When you find something new, there are fewer people doing it and it’s easier to stand out. Neistat says to start and to do it everyday. You need a lot of repetitions.  Malcolm Gladwell gave this same advice to people who want to write. Write for a newspaper, Gladwell says. It will force you to do many things, one of which is to get used to writing a huge volume of stuff.

Practice being the best version of you. And for pete’s sake, make sure you define success as something besides fame or money.

Who is successful?

“My grandmother,” Neistat says, “she loved tap dancing and didn’t stop until the day before she died.” Here again, Neistat inverts the question. Rather than think of success as the time spent doing what you enjoy, think of it as the time not spent doing what you dislike. Even the best of things won’t be perfect. 

I like this idea. Seth Rogen and Evan Goldberg both said that making movies isn’t all fun and games. It’s some fun and games, but there’s still work. They’ve applied Neistat’s idea of “less-suckiness” to work by creating a more relaxed work environment. 

Remember, a perfect job is a fallacy. Austin Kleon makes the art he wants to make, speaks across the country, and has written two best-selling books. When James Altucher suggested he was doing what he loved, Kleon stopped him. “I have to push back a little on that,” he said, “every job is still a job.” Jon Acuff had the same experience. Acuff quit the grind, but said he’s “doing a lot of stuff you wouldn’t consider dreamy.”

What success isn’t.

Success isn’t fame, or money. People don’t get this, Judd Apatow said. “It’s hard for people to understand what it’s like to give up all anonymity.”

Bill Murray added:

“I always want to say to people who want to be rich and famous: ‘try being rich first’. See if that doesn’t cover most of it. There’s not much downside to being rich, other than paying taxes and having your relatives ask you for money. But when you become famous, you end up with a 24-hour job.”

But then Murray stops short because it’s not about the money either. T. Harv Eker said that he thought money would make him happy. He got a lot of money, but wasn’t much happier. What is success?

What success is.

Success is loving the process. 

Chris Hadfield calls this creating win-win situations. For Hadfield it was about trying to get to space, but knowing the odds were slim. In his book, An Astronaut’s Guide to Life on Earth he writes:

“It’s probably not going to happen but I should do things that keep me moving in the right direction, just in case – and I should be sure those things interest me, so that whatever happens, I’m happy.”

Those things were the process. Hadfield literally aim for the moon, but enjoyed the work that he did on earth. That’s how to succeed. One a more practical level, Neistat shares 2 free tools anyone can use.

2 free tools.

No, this still isn’t about the right camera. There is no right camera. There are however, two free tools that anyone can use in life: good friends and some scarcity.

“I always try to surround myself with people smarter than I am,” Neistat says. Simon Rich did this too. When it was time to make his television show Man Seeking Woman, he hired people from all his favorite show like The Simpsons and The Office. “I want to feel like I’m barely keeping up,” Rich said.

It can be hard to ask for help. Amanda Palmer spoke (and wrote a book) about this. “If I learned anything from the surprising resonance of my TED Talk it was this: Everybody struggles with asking.”

But allies are out there and you need to find them. Nicholas Megalis found them for his Vines. Brian Koppelman has David Levien to write with.

The second free tool to use is scarcity. I was going to write a lack of money, but that would be conceited. Poverty as a muse sounds romantic. It’s insulting.

In her Harvard commencement speech J.K. Rowling addresses this better than I:

“They (Rowling’s parents) had been poor themselves, and I have since been poor, and I quite agree with them that it is not an ennobling experience. Poverty entails fear, and stress, and sometimes depression; it means a thousand petty humiliations and hardships. Climbing out of poverty by your own efforts, that is indeed something on which to pride yourself, but poverty itself is romanticised only by fools.”

But, there is something here. There’s something in scarcity, in bottoms, in failure. Rowling continued:

“So why do I talk about the benefits of failure? Simply because failure meant a stripping away of the inessential. I stopped pretending to myself that I was anything other than what I was, and began to direct all my energy into finishing the only work that mattered to me. Had I really succeeded at anything else, I might never have found the determination to succeed in the one arena I believed I truly belonged. I was set free, because my greatest fear had been realised, and I was still alive, and I still had a daughter whom I adored, and I had an old typewriter and a big idea. And so rock bottom became the solid foundation on which I rebuilt my life.”

The greatest living author had nothing. Just an old typewriter, a napkin, and a dream. She’s not the only one who tells this story. Scarcity forces people to be creative.

Kevin Kelly said “the lack of money is often an asset because it forces you to innovate. People with money will try to buy a solution, but because you don’t have money, you are forced to invent a solution.”

David Levien said the clipped train ride to work help him to write a better novel.

Tim O’Reilly said that they launched O’Reilly publishing because they didn’t have enough consulting work.

Dick Yuengling said that the brewer adapted because of prohibition.

Neistat says, “don’t blame it on the gear or the lack of resources because it’s never the resources that determine your success. It’s how you use what you have.”

This applies to time too. Austin Kleon and James Altucher both said they’ve seen many people who think that if they only had more time they could do the thing they dream of. It’s not true. Look at Andy Weir.

Weir was a software developer who found himself laid off from work. Between his severance package and savings he could take 3 years off and try to become a professional author. Did he succeed? No. Weir failed.

Out of money, he returned to work. Then the itch came again and he started writing again – all on the side. He wrote a book no one saw. Then the next began as a series of blog posts. People asked him for a format for reading it all at once, so he put it on the Kindle store. A few months later it over 30,000 copies were sold. After than Crown Publishing bought the rights. Then came the movie deal. Andy Weir had good friends that helped him write the book when it was blog posts and he had scarce time to write in. Good friends you’ll have to find on your own. Scarce time though, we have a tip for. It has to do with good signals, Van Halen, and candy.

Signals (what Neistat has in common with Van Halen).

“Everything is given one filter,” Neistat tells Ferriss, “is this good for me and my technology company (Beme), and if the answer is no it gets a pass.” Neistat’s signal is the question, “does this help Beme?”

These one-time filters are everywhere once you look for them:

Richard Feynman got so tired of choosing a dessert, that he resolved to always order chocolate ice cream. That was his dessert filter.

Barry Ritholtz said that he looks at the prices of classic cars as a signal for bull and bear markets, or if people say “ugh” to his trading ideas.

Ramit Sethi said that he looks for specific words when people interview with him.

Stephen Dubner called this, “teaching your garden to weed itself,” and wrote an entire book chapter about it.

Some banks figured out how to filter out dangerous marijuana growers.

The most famous of the signals might come from Van Halen.

The story goes, that when Van Halen was touring they had the latest and greatest light and sound rigs. There was just one problem. Each venue had a different person set them up. The guy who set things up in New York wasn’t the same guy that set things up in Charlotte. So, according to David Lee Roth, Van Halen introduced a wrinkle to their rider.

They said that among the other rock star accoutrements, they wanted a bowl of M&M candy with the brown ones picked out. Some people looked at this as divas being divas, but maybe not. Roth said they did this to see how closely a promoter read the rider. If they removed the brown M&M candy, they probably set up the equipment correctly.

Good signals save people decisions.

A business idea.

Sam Shank founder of Hotels Tonight said that all good business solve two things, time or money (ideally both). Neistat and Ferris both need help to save time interacting with people.

Someone could make a service that queued up responses over multiple channels (YouTube, Twitter, Facebook, Quora, etc.)  optimized for relevancy.

For example, if Neistat posted a video, the service would combine the video comments from YouTube and the Twitter comments into one timeline for Casey to respond to. Further, it would  prioritize by some metric; how long the person followed Neistat, how long they’ve been active on YouTube, how recently they had a question answered, etc. The service could filter out trolls and four letter words as well. 

Then when Neistat or Ferriss had time, they would go to that service and quickly respond to more fans.

Media suggestions.

Neistat say that his two favorite books are The Autobiography of Malcolm X and The Second World War by Keegan. He also recommends The Life and Death Colonel Blimp and Little Dieter Needs to Fly as videos to watch. Ferriss suggests people watch this clip from Miracle for inspiration to work harder.

Neistat suggests podcast listeners check out Make it Count and Draw my Life on YouTube. He says  Ben Brown and Fun for Louis are other good vloggers. Also, listen to Jonny Famous on Spotify.

Parting ways.

Neistat tells Ferriss that he would want a billboard that tells people to “be nice.” Adding, “being nice is really hard work.”

Thanks for reading. Really, thank you. This post was 3300 words. I’m a freelance writer and if you’d like to say “thank” via a $2 donation, you can donate here.